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Synthesis of Dihydrobenzoxazine‐Fused Spirooxazoline‐4‐ones via [3+2] Cycloaddition of Azaoxyallyl Cations with Vinyl Benzoxazinanones
Author(s) -
Kim Eunjin,
Mun Dasom,
Kim SungGon
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900517
Subject(s) - cycloaddition , chemistry , yield (engineering) , reaction conditions , in situ , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
An example of a [3+2] cycloaddition reaction between azaoxyallyl cations generated in situ and a variety of vinyl benzoxazinanones has been developed. This reaction provides an attractive method for the synthesis of spirooxazoline‐4‐ones based on dihydrobenzoxazines, which were obtained in good yield (up to 98% yield) with high diastereoselectivity (up to >20 : 1). The synthesized spiro‐bis‐ N , O ‐heterocycles can be used as building blocks toward the synthesis of other useful compounds.